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| CAS No.: | 94-62-2 |
|---|---|
| Name: | Piperine |
| Article Data: | 34 |
| Molecular Structure: | |
|
|
|
| Formula: | C17H19NO3 |
| Molecular Weight: | 285.343 |
| Synonyms: | 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]piperidine;FEMA No. 2909;Bioperine;Piperine (aliphatic);Piperidine, 1-((2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-;1-Piperoyl-piperidine;(E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]-piperidine;Piperidine,1-[(2E,4E)-5-(1,3-benzodioxol-5- yl)-1-oxo-2,4-pentadienyl]-;N-[(E,E)-Piperoyl]piperidine;Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-, (E,E)- (9CI); |
| EINECS: | 202-348-0 |
| Density: | 1.211 g/cm3 |
| Melting Point: | 131-135 °C(lit.) |
| Boiling Point: | 498.5 °C at 760 mmHg |
| Flash Point: | 255.3 °C |
| Solubility: | 40 mg/L (18 °C) inwater |
| Appearance: | slightly yellow powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 21/22 |
| Safety: | 36/37 |
| PSA: | 38.77000 |
| LogP: | 2.93510 |
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| Conditions | Yield |
|---|---|
| With Aliquat 336; potassium carbonate In toluene at 90℃; for 10h; | 95% |
| With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dimethyl sulfoxide 1) 15 min, 25 deg C 2) 2 h, 60-65 deg C; | 88% |
| Stage #1: piperonal With sodium hydroxide In water; dimethyl sulfoxide for 0.5h; Stage #2: 1-crotonoylpiperidine In water; dimethyl sulfoxide at 20℃; | 75.3% |
| With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dimethyl sulfoxide at 60 - 65℃; for 2h; Product distribution; various solvents; | |
| With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; dimethyl sulfoxide at 25 - 30℃; | 89 g |
| Conditions | Yield |
|---|---|
| Stage #1: piperic acid With thionyl chloride In dichloromethane at 20℃; Schlenk technique; Stage #2: piperidine In dichloromethane at 20℃; for 1h; Schlenk technique; Inert atmosphere; stereoselective reaction; | 95% |
| With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 8h; | 93% |
| With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20 - 25℃; for 1h; | 90% |
| With dmap; dicyclohexyl-carbodiimide Amidation; | 72% |
| With dmap; dicyclohexyl-carbodiimide In dichloromethane for 18h; Inert atmosphere; | 71% |
- 110-89-4
piperidine
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Bestmann ylide
- 58095-77-5, 14756-00-4
(E)-3,4-methylenedioxycinnamaldehyde
- 94-62-2
Piperine
| Conditions | Yield |
|---|---|
| In tetrahydrofuran for 24h; Heating; | 90% |
| Conditions | Yield |
|---|---|
| With dipotassium peroxodisulfate In water at 100℃; for 0.166667h; Microwave irradiation; Green chemistry; | 83% |
- 736947-76-5
1-[(E)-3,4-(methylenedioxy)cinnamylsulfonyl]acetyl-piperidine
- 94-62-2
Piperine
| Conditions | Yield |
|---|---|
| With aluminum oxide; potassium hydroxide; dibromodifluoromethane In dichloromethane at 20℃; for 1h; | 82% |
| Conditions | Yield |
|---|---|
| Stage #1: 3,4-methylenedioxy-trans-cinnamic acid With N-Bromosuccinimide; tetrabutylammonium trifluoroacetate In 1,2-dichloro-ethane at 20℃; for 4h; Decarboxylation; bromination; Hunsdiecker reaction; Stage #2: N-acrylpiperidine With palladium diacetate; triphenylantimony; triethylamine In 1,2-dichloro-ethane for 20h; Heck reaction; | 51% |
| Conditions | Yield |
|---|---|
| With palladium diacetate; triethylamine; triphenylphosphine; lithium chloride In acetonitrile at 70 - 80℃; for 18h; | 38% |
- 67911-75-5
(E)-5-(3-bromoprop-1-en-1-yl)benzo[d][1,3]dioxole
- 136055-33-9
N-<1-oxo-2-(3,6-diisopropyl-2-pyrazinylsulfinyl)ethyl>piperidine
- 94-62-2
Piperine
| Conditions | Yield |
|---|---|
| With potassium diisopropylamide 1.) THF, hexane, RT, 1 h, 2.) THF, hexane, reflux; Yield given. Multistep reaction; |
| Conditions | Yield |
|---|---|
| 1.) BF3OEt2 in refluxing toluene; 2.) oxidation (m-chloroperbenzoic acid, CH2Cl2,-78 grad C); 3.) reflux in toluene; Yield given. Multistep reaction; |
- 104683-09-2
Acetic acid 1-(benzenesulfonyl-benzo[1,3]dioxol-5-yl-methyl)-4-oxo-4-piperidin-1-yl-butyl ester
A
- 94-62-2
piperine
B
- 94-62-2
Piperine
| Conditions | Yield |
|---|---|
| With potassium tert-butylate In tert-butyl alcohol for 12h; Ambient temperature; Yield given. Yields of byproduct given; |
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Chemistry
Molecular Structure of Bioperine (CAS NO.94-62-2):
IUPAC Name: (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
Molecular Formula: C17H19NO3
Formula Weight: 285.34
Melting point: 131-135 °C(lit.)
Flash Point: 255.3 °C
Boiling Point: 498.5 °C at 760 mmHg
Density: 1.211 g/cm3
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 38.77 Å2
Index of Refraction: 1.614
Molar Refractivity: 82.14 cm3
Molar Volume: 235.4 cm3
Surface Tension: 51 dyne/cm
Enthalpy of Vaporization: 76.67 kJ/mol
Vapour Pressure: 4.5E-10 mmHg at 25°C
FEMA: 2909
Water Solubility: 40 mg/L (18 oC)
Stability: Stable. Incompatible with strong oxidizing agents.
EINECS: 202-348-0
Product Categories: Alkaloids; Biochemistry; Pyridine Alkaloids
InChI
InChI=1/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
Smiles
c12c(ccc(c1)\C=C\C=C\C(N1CCCCC1)=O)OCO2
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| hamster | LD50 | intraperitoneal | 105mg/kg (105mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Toxicology Letters. Vol. 16, Pg. 351, 1983. |
| mouse | LD50 | intramuscular | 400ug/kg (0.4mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Toxicology Letters. Vol. 16, Pg. 351, 1983. |
| mouse | LD50 | intraperitoneal | 43mg/kg (43mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Toxicology Letters. Vol. 16, Pg. 351, 1983. |
| mouse | LD50 | intravenous | 15100ug/kg (15.1mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Toxicology Letters. Vol. 16, Pg. 351, 1983. |
| mouse | LD50 | oral | 330mg/kg (330mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Toxicology Letters. Vol. 16, Pg. 351, 1983. |
| mouse | LD50 | subcutaneous | 200mg/kg (200mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Toxicology Letters. Vol. 16, Pg. 351, 1983. |
| rat | LD50 | intraperitoneal | 34mg/kg (34mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Toxicology Letters. Vol. 16, Pg. 351, 1983. |
| rat | LD50 | oral | 514mg/kg (514mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Toxicology Letters. Vol. 16, Pg. 351, 1983. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Hazard Codes: 
Xn
Risk Statements:
22: Harmful if swallowed
21/22: Harmful in contact with skin and if swallowed
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:
22: Do not breathe dust
24/25: Avoid contact with skin and eyes
36/37: Wear suitable protective clothing and gloves
36: Wear suitable protective clothing
WGK Germany: 3
RTECS: TN2321500
Hazard Note: Irritant
HS Code: 29399990
Poison by ingestion and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Specification
Bioperine , with CAS number of 94-62-2, can be called (2E,4E)-5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-on ; (E,E)-1-[5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl]piperidine ; 1-(5-(3,4-Methylenedioxyphenyl)-1-oxo-2,4-pentadienyl)piperidine ; 5-(1,3-benzodioxol-5-yl)-1-piperidinopenta-2,4-dien-1-one ; Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)- ; Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-, (E,Z)- .